[HenryMelton]

For a few weeks now, every time I sync my iPhone, one of the stages is Optimizing 10 photos, even though I haven't added any photos to my iPhoto library. I suspect that there are ten photos of some type that the sync process can't handle, but I haven't changed anything that I am aware of. I can't seem to find any messages in the logs or see any corrupted files in my library.

Does anyone have any pointers that could help me find the culprits?

[HenryMelton]

After investigation, I discovered that I had 13 photoshop psd files in my iPhoto library. Ten of those were created by Photoshop CS2 and three were from several generations back. I duplicated one of the recent ones and on the next sync I got 11 photos being optimized. I then exported all the suspect psd files out of iPhoto and replaced them with full sized tiffs. After an initial optimization of the tiffs, there is no longer any endless optimizations.

So iPhoto/iPhone has some bug regarding recent vintage photoshop files.